Symmetry and coplanarity of organic molecules affect their packing and photovoltaic properties in solution-processed solar cells

Shang Che Lan, Putikam Raghunath, Yueh Hsin Lu, Yi Chien Wang, Shu Wei Lin, Chih Ming Liu, Jian Ming Jiang, Ming-Chang Lin, Kung-Hwa Wei*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

35 Scopus citations


In this study we synthesized three acceptor-donor-acceptor (A-D-A) organic molecules, TB3t-BT, TB3t-BTT, and TB3t-BDT, comprising 2,2'-bithiophene (BT), benzo[1,2-b:3,4-b':5,6-d″]trithiophene (BTT), and benzo[1,2-b;4,5-b'] dithiophene (BDT) units, respectively, as central cores (donors), terthiophene (3t) as π-conjugated spacers, and thiobarbituric acid (TB) units as acceptors. These molecules display different degrees of coplanarity as evidenced by the differences in dihedral angles calculated from density functional theory. By using differential scanning calorimetry and X-ray diffractions for probing their crystallization characteristics and molecular packing in active layers, we found that the symmetry and coplanarity of molecules would significantly affect the melting/crystallization behavior and the formation of crystalline domains in the blend film with fullerene, PC61BM. TB3t-BT and TB3t-BDT, which each possess an inversion center and display high crystallinity in their pristine state, but they have different driving forces in crystallization, presumably because of different degrees of coplanarity. On the other hand, the asymmetrical TB3t-BTT behaved as an amorphous material even though it possesses a coplanar structure. Among our tested systems, the device comprising as-spun TB3t-BDT/PC61BM (6:4, w/w) active layer featured crystalline domains and displayed the highest power conversion efficiency (PCE) of 4.1%. In contrast, the as-spun TB3t-BT/PC61BM (6:4, w/w) active layer showed well-mixed morphology and with a device PCE of 0.2%; it increased to 3.9% after annealing the active layer at 150 °C for 15 min. As for TB3t-BTT, it required a higher content of fullerene in the TB3t-BTT/PC 61BM (4:6, w/w) active layer to optimize its device PCE to 1.6%.

Original languageEnglish
Pages (from-to)9298-9306
Number of pages9
JournalACS Applied Materials and Interfaces
Issue number12
StatePublished - May 2014


  • bulk heterojunctions
  • crystallization
  • organic solar cell
  • solution-processed small molecules


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